title: Anti-inflammatory alkaloids from the stems of Picrasma quassioides BENNET.
abstract: During further chemical and biological investigations of Picrasma quassioides BENNET, four new bis-β-carboline alkaloids, quassidines E-H (1-4), and three new β-carboline alkaloids, canthin-16-one-14-butyric acid (5), 3-(1,1-dimethoxylmethyl)-β-carboline (6), and 6,12-dimethoxy-3-formyl-β-carboline (7), were isolated from its anti-inflammatory CHCl(3)-soluble fraction. Structures of new compounds were elucidated and characterized by MS and NMR analysis. A plausible biogenetic pathway for quassidine E (1), the first bis-β-carboline alkaloid in which a canthin-6-one moiety and a β-carboline moiety were connected together by a single carbon-carbon bond from the nature, was proposed. Quassidines E-G (1-3) showed potent inhibitory activity on the production of nitric oxide (NO), tumor necrosis factor α (TNF-α), or interleukin 6 (IL-6) in mouse monocyte-macrophage RAW264.7 cells stimulated by lipopolysaccharide (LPS). Analysis of anti-inflammatory activity of all β-carboline and bis-β-carboline alkaloids from P. quassioides showed that the carbonyl groups or double carbon-carbon bonds at C-14 for β-carbolines and C-14' for bis-β-carbolines were bioactive groups for their in vitro anti-inflammatory activity. Structure-activity relationship of these compounds on inhibitory activity of the three inflammatory cytokines was discussed.
authors.affiliation: School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China.
authors.forename: Wei-Hua
authors.initials: WH
authors.lastname: Jiao
authors.forename: Hao
authors.initials: H
authors.lastname: Gao
authors.forename: Feng
authors.initials: F
authors.lastname: Zhao
authors.forename: Hou-Wen
authors.initials: HW
authors.lastname: Lin
authors.forename: Yu-Min
authors.initials: YM
authors.lastname: Pan
authors.forename: Guang-Xiong
authors.initials: GX
authors.lastname: Zhou
authors.forename: Xin-Sheng
authors.initials: XS
authors.lastname: Yao
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D015850:Interleukin-6 / Q000378:metabolism; D008070:Lipopolysaccharides / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008968:Molecular Conformation; D009569:Nitric Oxide / Q000378:metabolism; D032270:Picrasma / Q000737:chemistry*; D018547:Plant Stems / Q000737:chemistry; D013329:Structure-Activity Relationship; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors / Q000378:metabolism; D000093242:Interleukin-6 Inhibitors
chemical_list: D000470:Alkaloids; D000893:Anti-Inflammatory Agents; D015850:Interleukin-6; D008070:Lipopolysaccharides; D009569:Nitric Oxide; D014409:Tumor Necrosis Factor-alpha; D000093242:Interleukin-6 Inhibitors